Happily Ever After
by Shnorkel
Summary: Addison and Jake finally get it on but their first time is far from magical.    Roleplay Adapted


**DISCLAMIER: I do not own anything, yada yada yada, I am just an aspiring writer with a filthy mind who ships Jaddison like, so hard.**

**Addison, Jake, Private Practice, everything else, pretty much belongs to the devil. (Shonda Rhimes & ABC studios)**

**WARNING: There is nudity and STRONG sex scenes. It's purely smut.**

**DESCRIPTION:** Addison and Jake finally get it on, but their first time is far from magical.

Written by Shnorkel and Serena.

**Happily Ever After**

Jake ran his hands up her thighs a little, pushing her dress up with it and kissing her a bit harder. He couldn't help himself, she was just so sexy, he could completely lose himself in her but he did have self control and so he pulled back. "Addison." He said softly, as he slowly removed his hands. "I think we should stop now. Before it goes too far." He said softly. Addison had kissed him firmly, thoroughly enjoying the moment until he pulled away, her green eyes slowly opening and her lips forming a dissapointed pout. She didn't want things to go too fast, she didn't want things to stop but she was also a little nervous about their first sexual encounter. Her teeth slowly grazed along her bottom lip before she spoke softly. "I dont want to stop." It was so hard to stop himself, Addison was so amazing and he so wanted to have sex with her. The night had gone so well, the perfect date and sex would be such a great way to end it but he just didn't want to rush things. "I don't want to stop either." He said softly but he took a step back again. "I think...we should set a five date rule." He exhaled.

She probably would think he was weird, but honestly he just wanted to hold off in jumping into bed with her. Addison did that a lot; he knew that but Jake wasn't like that and he wanted to make sure this was what she wanted. "So five dates...and then if things are going as well as tonight then.." He trailed off. She knew what he was saying. He looked at her, waiting for her response and hoping she wouldn't be upset or angry. Addison watched as he pulled back and her hands came to her thighs, pulling her dress down a little. This was probably the third time he had turned her down for sex, it was such a kill. She was pouting as she got down from the counter, her heels clicking against the floor. "Five?" Her red brows arched highly as she looked at him. He seriously wanted to wait five whole dates until they could have sex? "Is, is it because you've seen my vagina in a medical way?" She groaned softly, of coarse that would turn him off having sex. "So, you need five whole dates before you can psych yourself into having sex with me?" She spoke softly, her finger drawing patterns over the counter top as her insecurities shon through. She never used to be insecure, but since being with Sam, she was a little different, she had insecurities now that she never used to have.

Jake could tell he had hurt her a little and he felt bad. He didn't want to hurt her in anyway, that was why he didn't want to rush into anything. He wasn't the kind of guy to just have sex at any time. For him it was a physical act that involved emotions, unlike other men who just thought of it as physical. It wasn't like that and he wanted more than anything to have sex with her but she had no long been broken up with Sam and shoving her face with bacon cheese burgers, getting drunk and trying to sleep with him. He was being considerate, not nasty. He laughed at her comment and shook his head. "Well, at first yes but now, no. That's not the reason. I could easily see your vagina in a ...sexual way." He admitted. "Addison, stop." He exhaled. "I don't need five dates to psych myself into having sex with you. I want to have sex with you…trust me. I really do." He ran his hand up over his face and through his hair as he looked at her before stepping forward and placing his hands on her forearms gently. "You're gorgeous. Having sex with you is not a problem. I just don't want to rush things." He tried to explain. "Why do we have to have sex on the first date? Won't it be even better if we wait until the fifth?" He placed his hand under her chin and tilted her head so she was looking at him. "Can you understand?" He asked softly.

Jake knew all the right things to say and he had her pout dissapearing and a small smile coming back to her lips as she nodded slowly. "I understand, your right." She understood his logic and she was so glad that her vagina wasn't an issue at all. "Fifth date." She confirmed. "Fifth date." Jake repeated, a smile curving onto his lips as she agreed. He smiled, relieved she understood where he was coming from. He pressed a kiss to her cheek and then pulled back ."Next date, your place." He laughed. He didn't expect her to cook - she couldn't really, but that was fine.

The fifth date seemed to come very slowly, but finally it had arrived. It had been about a month and a half since the first date and though both of them assumed it would have happened by now - unfortunately they were doctors and many dates had to be postponed. They had already postponed this fifth date twice but tonight Jake hoped like hell Addison wouldn't get called away, and neither would he. They deserved this - they had been dating a little while now, having lunch every day and everything (though they weren't counted as 'dates'). Jake had invited Addison to his place. Another home cooked meal, a lamb roast. It was cold out though so the fire was on and he had set up a table in the living room with candles, he would dim the lights and all. Upstairs he had sprinkled rose petals on the floor and a little on the bed. He had a bottle of champagne waiting in a cooler up in the bedroom, he had a condom in case she would prefer that. He was ready, they had waited and they deserved this. The roast beef he had made was nearly ready, served with roast vegetables and of course a glass of Addison's favourite red wine. He had dressed in navy blue pants, his leather shoes on and a grey shirt with a vest over top. His hair was styled and everything was perfect. He was pacing a little, waiting for Addison and hoping to god the phone wouldn't ring.

Addison was nervous, butterflies fluttering around in her stomach as she prepared for their fifth date. This was it. This was the night. They deserved this though and she was excited at the same time. She loved the time she spent with Jake, he was amazing. She straightened her long red hair before adding slight curls, she made sure her make up was perfect, her green eyes popping and seeming vibrant, her lips coloured a deep red. She chose dark coloured panty hose under her black designer dress and pumps, helping to keep her warm and stylish at the same time. She had a designer jacket on as she rushed into Jakes' house and out of the cold weather outside. "Jeesh its cold out there." She spoke with a soft laugh before offering a smile to Jake. "Hey." She spoke fondly, her heart skipping a beat as she saw how damn good he looked. "You look great." She complimented.

At the sound of Addison's voice, Jake turned and smiled. She was here. "It is, that's why I've got the fire on" He grinned before looking over her. "You you look...breathtaking" He told her as he walked over and kissed her lightly, Addison's hands settling on his hips as she kissed him back. "You hungry now? Dinner should be ready." Jake smiled. "Glass of wine?" He added as he moved over to the kitchen. "Mm thank you." She smiled and took off her jacket, hanging it up before following him to the kitchen. "Starving, can we eat by the fire?" Her heels clicked along the floor until she stopped and leant back against the kitchen counter, watching him.

"Of course. The table is set up by the fire; candles and all" He said as he walked into the kitchen and poured her a glass of wine handing it to her and pouring his own. He took a sip before he began to get the dinner out of the oven and prepared to eat. "Thank you." Addison took the wine, taking a sip. "Mm my favourite." She smiled, he remembered. "Need help with anything?" She offered, happy to help. "No, everything is done so you go sit down and I'll be right there" He told her. Addison would have been happy to help but it was so nice to not have to be the one making sure everything was done, she sat down at the table, a leg crossed over the other and waited for him to join her. Eveything was so easy and nice between them. They had great chemistry and enjoyed each others company. He felt they were perfect for each other. It didn't take long for him to be at the table, their meals in front of them. "Enjoy" He smiled.

"Smells amazing." She wasted no time in digging in which shouldn't surprise him because he knew by now how much she loved food. She moaned softly, the food was delicious, which didn't surprise her because Jake was always an amazing cook, where as she just ordered Chinese food or pizza when the dates were set at her house. She smiled at him, really enjoying her dinner and it was warm by the fire.

Jake was pleased there didn't seem to be any tension because it was the fifth date. It was like as soon as he saw Addison his nerves had evaporated and they were just so happy and chill it made things great. "Thank you" He smiled as she complimented his cooking again. He was eating his dinner and sipping his wine, enjoying the evening. "How was your day?" He asked her as he cut his meat. Addison smiled, rarely did she get asked by boyfriends how her day was. "It was good. I delivered twins, theyre both healthy and doing good." She spoke before sipping her wine. "How was your day? Knock anybody up?" She asked with a playful grin before continuing to eat. "Well good job" Jake grinned. He didn't think the question was much but he was interested to know. "Well its very possible yes but we will find out in a few weeks" he chucked. That would be an odd question if he wasn't a fertility doctor, it amused him.

Addison was definitely the best in her field so it was really no surprise she delivered two healthy twins. She continued to eat, chuckling softly with him, liking that she was able to amuse him. She was soon finishing off her food with a very content moan of appreciation. "God that was so good." She smiled as she took a sip of her wine to wash down her dinner. Jake liked to call Addison the Meryl Streep of medicine, and it was very true. He was enjoying his dinner too, and soon enough he was finished like Addison, placing his cutlery down. "It was delicious." He agreed, even if he did say so himself. He sat back in his chair and picked up his wine, drinking some back and exhaling to wash his dinner down.

Addison smiled to her boyfriend, that's what he was right? Her boyfriend. Yeah, of coarse he was. She finished her own wine. "Thank you, dinner was lovely, your such a great cook." She had a few nerves about the fifth date, the plans they had made, but it wasn't like it was her first time, she was very experienced and skilled with sex, she loved sex. But it was still a little nerve racking. It was the fifth date. They both knew what that meant and Jake was excited and nervous. There was no need to be really but there was always that fear that their great chemistry wouldn't cross over to the bedroom. He knew Addison was probably more experienced than him but he considered himself good in the bedroom. He soon stood up and took Addison's hand, pulling her up and moving to the couch where he sat and motioned for her to sit next to him. "I know you know what this date is. I thought we should talk before...like where we stand with each other and what we want to be to each other." He said simply hoping she didn't think he sounded like a female.

Addison took his hand, following him in to the loungeroom, and when they sat, she leant in against him, crossing one leg over the other, her hands smoothing over her short dress and her thighs that were covered by dark coloured panty hose. He really made her swoon, a guy that cared about talking and feelings was a rare occurance, or they were gay but she was pretty sure Jake was one hundred percent straight, he was just perfect. She didn't even care if all this perfection was to make up for a small penis, which she doubted was small but was still curious. "Talking is good." Jake nodded. He agreed that talking was good. He didn't see the point in not talking and leaving everything to be guessed. Talking made for a good relationship and that was what he wanted with Addison. He wanted to make sure they were always on the same page at all times, Addison wouldn't ever have to wonder about how he felt about her and he hoped it would be vice versa. She smiled, wriggling her toes and letting her high heels fall from her feet and to the floor before tucking her legs underneath her. "Well, we're dating, so.. I mean, we're exclusive right? Not seeing anyone else, this is real, right?" Her green eyes peered at him curiously, hopefully. "Exclusive, yes." He agreed. "I don't want to see anyone else. It's real Addison. It's very real." He aid as he took her hand. He knew that much was true.

Leaning into him, Addison looked up at Jake with a smile, placing her hand on his chest. "So, I can call you my boyfriend? And we can tell people about us?" God he made her incredibly happy. Jake placed his hand onto hers and nodded. "I would love to be called your boyfriend and we can tell people whenever you want to." He added, more than happy to let everyone know that Addison was his woman. Addison smiled happily, very happy and proud to be able to say that Jake was her man, she was very proud of that. "Mm I want to tell people, I want to show off my amazing boyfriend." She smiled as she leaned in and kissed his lips softly. "Perfect." He said softly. There was nothing more perfect than this moment. Addison Forbes Montgomery was his girlfriend. He kissed her back softly, loving the touch of her lips. He had no idea how Sam would react to this but he didn't care. They would deal with him.

Sam was the furtherest thought from her mind, Addison didn't care about Sam, she only cared about Jake right now. And kissing him. She kissed him a little firmer, her hand coming up to cup his cheek softly, her green eyes closed as she enjoyed the contact. The kissing was the start of what was going to happen. This time he wouldn't pull back and he would continue out. He placed his hand on her thigh and kissed her a little harder. Addison kept their lips connected as she shifted, moving to straddle his waist, sitting on his lap with a leg either side of him as her hands cupped his cheeks and she kissed him deeply, her tongue pushing into his mouth to flick against his. As soon as Addison was straddling him, his hands moved to her hips and he began to kiss her a little deeper too. His lips parted and his tongue moved to meet hers, kissing her firmly and groaning a little.

They both knew what the fifth date meant, her hips pressed into his a little as she massaged her tongue against his, her fingers slipping through his hair. Her dress was now pushed quite high up her thighs to allow the flexibility of straddling his waist. If she wasn't wearing pantyhose he could probably see her silky, lacy purple panties. Her panties were always a sexy kinda, cheeky cut. Not quite a g-string but no where near full underwear. It was classy and sexy at the same time with out getting slutty. Jake already knew this though from all those times he had injected her with her hormone injections and no doubt enjoyed it.

Jakes hands roamed her thighs before moving from her pantyhose clad thigh and traveling up her waist a little. He kissed her a little harder, accidentally knocking his teeth with hers but he just pushed past it and continued to move his hands up her body. Addison crinkled her nose a little as their teeth knocked together but she kept kissing him, moving past it. She loved the way his hands were roaming her body, it felt really good. Her hands moved to rub against his chest, slowly starting to undo his shirt, fumbling with his buttons awkwardly. Jake kept on kissing her, feeling her struggling with the buttons on his shirt he looked down, bumping heads with her and groaning a little before attempting to kiss her and getting her eye. Addison's hands moved from his shirt, flying to her head with a groan as they're heads bumped together, then her eye twitched as he kissed it by accident. "Should we go upstairs?" He asked, figuring maybe they could get in a better flow on the bed or something. "Good idea." She nodded in agreement, this was awkward, hopefully things could get better if they were in bed. She shifted to stand up but her knee accidentally hit him in the groin, not too hard, but hard enough. She quickly stood. "Oh god I'm so sorry, oh god." Why was she so clumbsy and letting nerves get to her!

Jake groaned a bit and cupped his groin as she kneed him enough to hurt a bit. "It's fine, I'm fine" He exhaled as he slowly stood up. "Come on" He smiled. He had the rose petals and everything on the floor of his bedroom maybe the mood would be set better and they could relax. Addison looked very apologetic as he cupped his groin and she kissed his head softly. "God I'm sorry." She could kiss it better for him once the got to the bedroom and actually got out of their clothes. She took his hand as he lead her up to the bedroom and she smiled when she saw the rose petals. "Oh Jake, that's so sweet." He was so romantic, she loved that, she hoped it would last.

"You're welcome." He said softly as he removed his shirt. Maybe it would be easier that way. He dropped it to the floor and his stomach and chest was revealed to her. He did work out, his broad shoulders were easily seen and his toned chest and stomach - of course he was a man in his forties and he wasn't twenty-one anymore but he still had a pretty decent body. He moved towards her and smiled as he pulled her close. "Let's try this again." He whispered, leaning in and kissing her. "Mm." Addison smirked as her hands smoothed over his toned stomach and chest, they're lips meeting again in another soft, romantic kiss, her sea green eyes fluttering shut as her hands moved down to his belt buckle, pulling it open and pulling the leather through the loops quickly, but as it came out, the tail whipped her thigh, causing her to gasp and bite his lips softly as she grabbed her thigh, a nice red welt forming beneath her panty hose. "Shit." She mumbled as she pulled back a little. "I'm sorry.." god, what else could go wrong?

Things seemed to be going well at first and Jake was glad, but it didn''t take long for things to become messy again. "Addison!" he exclaimed. "Oh god, are you okay?" He asked as his belt whipped her thigh, leaving a decent mark that would have hurt he was sure. Addison tossed the belt to the floor with a groan, her hand rubbing over the mark and offering him an awkward smile. "I'm fine.." She pecked his lips softly, really wishing that things would go better for them. She kissed him more firmly before stepping back pulling her dress up a little and grasping her pantyhose, trying to pull down the tight material, getting it down her thighs and past the nasty red welt that had left her skin raised and agitated, the skin slightly broken, it stung, but she was fine. Jake bent down to help her with her pantyhose that seemed to not want to come off, once again colliding with her head and he stood right up. "Ah, sorry." he mumbled, rubbing his head before exhaling. He had no idea why he was being like this, so awkward and fumbling around. Addison groaned loudly and quickly snapped up, holding her head again, that was really gonna bruise by tomorrow. "Ow." She pouted. This was awkward, sex was never this awkward for her, she was good at sex, well usually any way. She was determined though. She bent down and tugged her pantyhose down some more until they were around her ankles, but she lost her balance and tripped over them, falling down, face first on the bed - atleast it wasn't the watched her and pursed his lips. This wasn't really going to plan. He wasn't like this usually either but he was getting a bad feeling from it. "Oh!" He gasped as she fell but luckily landed on the bed. "Unzip me?" She groaned as she lifted her head from the bed, her red hair a mess but she blew it out of her face. She must have been really unattractive right now. He chuckled as he sat down. "Sure." he smiled as he began to unzip her only having it catch and break off not even half way down. "It broke!" He exclaimed in shock. Why was this happening?

Addison was hoping that this wouldn't ruin the mood, maybe once they were naked and making out the rest would fall into place, they'd have amazing sex, what could go wrong during sex? The zipper caught and she cried out in annoyance. "Rip it!" She used her feet and removed the rest of her panty hose and she looked up at Jake, hoping he could actually rip her dress. Sam was huge and muscular, extremely well built and fit, he was massive, he had always ripped her clothing during sex, even Derek liked to rip her clothing, surely Jake could. Jake raised an eyebrow and as soon as she said to rip it he did just that. The material was easy to rip, the tear heard through the room. "There we go." He smirked as her whole back was revealed to him, her panties looked so amazing. Her body was incredible. Addison moaned as he tore the fabric, that really turned her on. "You're so sexy." He whispered as he pressed a light kiss to her back. Her back arched slightly as he kissed her bare back. Her purple panties showed off a lot of her nice ass and they matched her push up bra that really displayed her breasts, she wasnt exactly well off in the breast compartment, she'd like them to be a bit bigger, but she did alright, atleast she wasn't completely flat chested. "Mm, so are you."

Jake felt his cock begin to stir, her whole body was just amazing and she certainly turned him on that was for sure. He trailed his hand along her side, outlining her body and biting her lip as he looked her over and smirked. He began to work on her bra, but the clasp seemed to be jammed as well. Usually it would take just a second to unclasp it but right now he was using two hands and trying to pry it open. "What is this some kind of breast jail." He muttered to himself. Addison grazed her teeth along her bottom lip as she waited patiently for him to get the clasp, laughing softly at his comment. "Hang on." She got up, kneeling and pushing her dress down off her body, removing it and pushing it aside. She tried to get the clasp herself but it wasn't budging so she decided to try and take her bra off like you would a t-shirt, getting a little stuck with a groan but soon enough being free of it and tossing it aside, her perky little breasts exposed for him, her small, puffy, pale pink nipples hardened in the cold air and she bit her lip a little. Jake's eyes settled on her bare breasts in front of him. They were amazing, of course. "Wow" He mumbled his cock very much reacting to her now as he began to harden within his pants.

Addison's lips curved into a smile at his reaction, that was definitely a good reaction. She was just in her tiny panties now, so her hands came to his pants her fingers popping open the button and tugging down the tough zip which took her a little while but she was soon tugging down his pants. Her panties were damp with fresh arousal, butterflies in her stomach as she got closer to revealing his cock. She subconsciously licked her lips at the thought of what exactly his cock was going to be like. Jake couldn't take his eyes off her, she was stunning. He rested back a little as she began to undo his pants, not too much trouble now as his pants soon were off and he was in his boxers, his large bulge showing through and still growing. Addison finally got his pants off and his bulge was very noticeable through his boxers, her teeth grazing along her bottom lip slowly, a horny habit. She slowly dipped her fingers into the waist band of his boxers and pulled them away from his cock before pulling them down, to avoid bending him or hurting him. His shaven and circumcised cock sprung free and she was moaning as more moisture lubricated her pussy. "Oh wow." His cock was maybe slightly above average, shaven and circumsized. He was big, he was really thick. She loved that he was shaven and circumsiced cocks were probably her favourite because she loved blowjobs and she didn't have to worry about pubic hair getting in the way or ripe foreskin if her boyfriend hadn't recently showered. "Mm." Yeah, he was virtually perfectly and he had an amazing cock. She pushed his boxers down the rest of the way and tossed them aside before she gently, tentatively, took a hold of his large erection, starting to stroke him up and down slowly.

Jake wasnt too nervous about his cock being revealed. He was quite confident and happy with his size. Sure he wasn't the biggest but he was decent and that was enough. Addison had seen bigger, but she didn't think she had ever had bigger, she was excited, she hoped her tight pussy would adjust to him quickly with minimal pain. He smirked as she laid her green eyes on him and her expression said it all. She liked what she saw, just as he liked what he saw of her. He couldn't wait to see her pussy...he had seen it before but that was very different. This time he would see it in a sexual way and that was so much better. "Oh god" He mumbled as Addison took hold of his erection, her simple touch basically having him fully erect. Her hand felt amazing over around his length and he exhaled deeply. "That's so good" He whispered. "Take off your panties" He said softly; being able to look at her pussy as she stroked him would be so amazing before they had sex. She was stroking his cock, really enjoying it, liking the way he became fully erect under her touch, but then he wanted her panties off so she released his erection and she stood. She hooked her fingers through her panties, bending over and slowly pulling them down and tossing them aside. Her pussy was freshly shaven in preparation for tonights activities, making her really smooth, her plump lips a light shade of pink, her inner lips slightly more out then her outter. He had already seen her pussy many times, but that was medically, this was different. Jake watched as she removed her panties and his brown eyes got a good look at her amazing pussy. Now she got back on her knees and she grasped his cock again, dipping her head to swipe her tongue over his sensitive tip with a soft moan. His cock twitched in arousal as she returned to the bed and her hand returned to his cock. He reached over, pushing her legs apart so he could see her pussy, her wetness glistening and he moaned as soon as he felt her tongue. That he had not expected and he bucked his hips a little uncontrollably. "Addison" He mumbled tilting his head to look at her pussy and glance back to her mouth on his cock.

Addison moaned softly as she created a light suction with each kiss she started to trail down along his length, her green eyes peering up at him as she watched him admiring her glistening wet pussy, she was so wet and ready, but she absolutely loved blowjobs. Jake watched her in pure pleasure. She was amazing, to say the least. He groaned out softly reaching between her legs easily from the position they were in and coating his fingers in her wetness as he slid them down her pussy length and inside her silky folds. Addison groaned softly against his cock as she started to take more of his length into her mouth, sucking and twirling her tongue around him. "Mm." She moaned, squirming her hips as she felt his fingers on her folds. She was really wet, which was to be expected, she had been waiting for this night for ages and now she had his huge erection in her mouth. Jake was definitely enjoying himself and Addison was extremely skilled with her mouth it appeared. His two fingers lightly moved in a stroking motion inside her folds feeling her arousal and he groaned more intensely as she worked his cock with her mouth. His tip was very sensitive of course and her tongue had him bucking his hips as he moved his body a little, pushing her legs apart and moving his hand to her entrance soon pushing two fingers into her slowly. Her back arched a lightly as Jake slowly pushed two fingers into her tight pussy, a moan slipping from her lips and vibrating against his cock, causing him to groan in pleasure. Jake was in so much pleasure; her mouth was magic and his fingers thrusted into her soaked pussy with a groan. He didn't want to stop but he also wanted to have sex. "Addison..Addison" He moaned softly but removed his fingers and lifted her head from his cock. "Do you want me to wear a condom?" He asked. He was just being considerate but no male actually liked condoms of course.

Addison really enjoyed blowjobs so she was dissapointed when he lifted her mouth off of his now saliva covered cock but then she grinned, knowing that sex was coming and she definitely wanted sex. "Mm, it's up to you." She didn't want a condom, nor did she think they needed one, she was pretty infertile, and she was off the hormone injections, for now, but she was also off of the pill. Jake knew all of this, he knew her body better than she probably knew it, he could decide for himself weather or not he wanted to take the minimal risk. She had had several failed IVF attempts so she highly doubted she would suddenly miraculously conceive naturally. Jake nodded as he said she didn't mind. "No condom then." He said softly. He was a male, a condom was a pain and plus the possibility of her getting pregnant was so low it was basically none and that was not anything to worry about. "As long as you don't mind." He double checked, in case she did actually want him to wear one. She got up on her knees, moving to lay on her back, her feet on the bed, her knees bent and slightly apart as she watched him, ready for him. She assumed that missionary with him on top would be their best option for their first time. Plus she was a little worried about his size. "Go slow, your reallybig, I've never had as big before.. And I'm really tight." She whispered softly, a little embarrassed, her cheeks turning a little pink, her hands slowly caressing her own sides as she grazed her teeth along her bottom lip. She was really wet, she was hoping for it to ease the process. He watched her as she got into position, the same position he had in mind for their first sexual encounter. It was probably easiest as they learned what one another liked. He began to move, hearing her words which were definitely ones a male loved to hear. He was big, length wise he was a bit above average but thickness he was much above average and of course erect it grew a few inches too. He smiled as he slowly moved so his body was hovering above hers, resting between her legs as he pressed a kiss to her lips. "Don't worry Addison. I'll be gentle." He said softly as he grabbed his cock and pumped it a little. "Let me know when you're ready." He whispered, pressing his tip to her entrance.

"It's better without latex." She whispered with a smirk, her hands coming to his chest as he hovered above her and kissed her lips. Her fingers smoothed over his chest, playing with his light chest hair, she liked chest hair as long as it was minimal. She kissed his lips before pulling back and watching as he pressed his thick cock to her entrance, making her bite down on her bottom lip and nod, telling him to go ahead. They still had a lot to learn about each others bodies and what they liked. Jake was about to learn that Addison was incredibly tight and that would cause him immense pleasure. That would probably mean that her previous boyfriends had cocks that were below average. Jake kissed her lips lightly and nodded. He really didn't want to hurt her. It reminded him of being a teenager though, two virgins and not wanting to hurt. He very slowly pushed the head of his cock into her entrance. She was tight, he could feel that instantly and his cock definitely stretched her walls a lot. He stopped, not going in any further right now and waiting for her to adjust and tell him to continue. Addison gasped lightly as his tip stretched her, her hips jolting in pain as her hands flew to his hips, stilling him. "Uh." She groaned softly, her beautiful features contorted in pain. Jake knew that he was hurting her and he frowned a little before pulling out slowly. "I'm sorry." He whispered, the last thing he wanted to do was hurt her. He dropped his hand down and began to rub her pussy slowly. Maybe she just needed some help to relax and be more aroused so he would be able to slide in a little easier. Addison instantly felt better as he pulled out. "It's okay, you don't have to be sorry." She spoke softly as she kissed his lips softly, her hips rolling slightly as he started to rub her plump pussy lips, her green eyes fluttering closed as she tilted her head back and enjoyed the pleasure. She was already very wet and turned on, but maybe she just needed more lubricant and to be slowly stretched by his thick fingers.

Jake tilted his head, his lips attaching to her neck and sucking lightly on the skin as he pushed her fingers into her, two at first and then three. He used them to stretch her walls lightly, thrusting them a bit as he sucked over her skin as he worked his fingers. Addison's thin lips parted in a moan, her back arching slightly as he pushed two fingers into her tight, wet pussy, his lips on her neck. She loved having attention played to a certain part of her neck and just below her ear, Jake would figure that out easily. She also liked two fingers in her pussy, it was a nice amount to fill her. His third finger was fine, it was a little uncomfortable at first but she grew accustomed to it, her hips wriggling as she moaned softly, a very similar moan to the moan she let out whilst eating ice cream. He really wanted to be inside her now, his cock throbbing after being removed from the extremely tight walls and he groaned lightly against her neck as he slowly added a forth finger. But then the fourth finger stretched her a little too far and was painful, making her wince, her hips stilling as her body stiffened a little. Of course he felt her reaction to the forth finger and knew he had hurt her once again so he removed the forth finger and continued with three deciding he would take his time not forcing his fingers into her. His lips slowly moved up as he began to suck lightly on her neck, just below her ear his tongue trailing along her skin lightly.

Addison relaxed again when the fourth finger was removed and he went slower, he had gone too fast, introducing too much too soon but now he was back down to three fingers and it was alright. She turned her head, he found that sweet spot below her ear and she flexed her toes, a low moan slipping from her throat, letting him know he had found her sweet spot. He knew straight away from her reaction that he had found her sweet spot and he smirked, sucking a little harder and already having left a few hickey's along her collar bone and neck. Her hand moved to cup his shaven balls lightly, starting to gently massage them in her palm, repaying the attention that he was paying her. He mumbled lightly as she cupped his balls and massaged him a little as he moved his fingers within her tight pussy. "M-maybe some lube will help.. Do you, do you have lube?" She managed to get her sentence out softly. He heard her words and nodded, the same thing was crossing his mind. He lifted his head and pressed his lips to hers softly as he pulled his fingers out gently and she instantly missed his touch as he pulled away, his fingers leaving her pussy and his lips detaching from her sweet spot. She put her knees down, spreading her legs but keeping them bent, her fingers moving down to slip through her folds and feel how wet she was, the lube certainly had to help. She just wanted him inside of her already, she hated it was taking this long and it was essentially her fault, she also knew that it would be this way for a quite awhile until she permanently adjusted to his thick size.. "I think I do." He said softly soon pulling away and heading over to the drawers where he pulled out a small bottle of lube and held it up to her before heading back. He hated that it was taking so long to get inside of her, and he felt like maybe this was all a sign or something but he wouldn't accept it. He would do whatever it took.

Heading back over towards his extremely sexy and naked girlfriend as he sat down between her legs and looked over her pussy. He hoped this worked because he didn't want to use a condom either. Opening the lube, he squirted it on her pussy and rubbed it in before putting some on his cock too. Addison bit her bottom lip and moaned very softly as he rubbed the lubricant into her pussy and then done the same to his cock, making both of them glisten. "Ready to try again?" He asked softly. She nodded. "Ready when you are." She agreed, shifting her legs again to allow him between them, she knew his cock must have been throbbing and she really didn't want him to get fed up and think that all of this hassle for a bit of sex wasn't worth it, she wanted him to stick around. Addison moved her hand between her legs, her fingers instantly coated thickly in lube as she used her index and middle fingers to spread her folds for him.

Jake did as she requested and he very slowly and carefully pushed his cock into her. Addison instantly groaned softly, stiffening a little as he pushed his head into her tight hole, she was so tight, the lube didn't change that, it just made it easier for him to get inside of her. "Uh." She frowned a little, but she wanted to be able to adjust and to get past the pain otherwise they just weren't going to get anywhere. His thickness stretched her walls and soon his length was buried completely inside her.

Jake was still but the simple act of pushing inside of her right walls was amazing and the pleasure was so intense with how tight she was. He groaned but he stayed still mostly. "You okay?" He whispered softly, his lips pressing against hers in a kiss. Addison kissed him back, mumbling against his lips. "Keep going." He needed to keep going so that she could get over the pain and adjust to his size, she was tense now, her hands braced against his hips, but she would ease up after he got moving and it didn't really matter if he came before her, she didn't mind at all, as long as he came. Jake nodded as he kissed her again and slowly began to move his hips. It was so good for him and he wanted Addison to have a good experience and so far things hadn't been exactly perfect like he had planned. Addison pulled her lips away from his, biting down on her bottom lip as he slowly began to thrust his length inside of her with the help of the lube. It was uncomfortable, he was very thick, she wasn't used to it, but surely she would adjust soon. "Just keep going." She whispered softly, her tight walls must feel amazing around his cock.

Jake's erection easily stretched her walls to a point they had never been stretched to before. Her hips were still, her face a look of concentration and discomfort but it would pass soon she hoped, it had to, Jake was perfect, she could actually love him, she was pretty sure she was already falling in love, he was amazing, so she had to do this, she had to be able to give him this, no matter how long it took for her to get used to it. Jake's hips continued to move gently, thrusting his cock in and out of her slick pussy slowly, god it was so pleasurable for him to have her be so tight. "You okay." He mumbled against her skin soflty. "Fine." She replied with a simple one word answer, her finger tips lightly brushing against his hips as his length buried within her extremely tight walls, knowing he must have been in immense pleasure which was quite a relief and a turn on.

Jake's lips found her sweet spot just below her neck, losing himself in her, sucking on the smooth skin whilst her green eyes opened, squinting a little up at the ceiling as her hips remained still whilst he moved in and out of her. Nobody liked a starfish during sex, she was usually very good at sex, she didn't just lay there, but tonight was not going as planned, she was still adjusting, her arms loosely wrapping around him. She had been really hoping for a first time like in the movies, but obviously that wasn't meant to be. If this was how it always was then Jake would have a problem but he knew Addison wasn't like this usually in bed - he didn't know from experience but he wasn't stupid. This was different though and he was happy for her to do whatever it took to feel okay. He hated knowing he was hurting her but he knew she would tell him to stop if she had too. He kept his body moving slow and steady ontop of her; his cock easily sliding in and out with the help of the lube. "Youre so tight" He groaned loudly. It felt so amazing for him and he only wish it did for her too.

Addison was just glad that it felt good for him, it must have felt amazing for him, she was so tight, guys loved tight, she oftened heard them saying 'the tighter the better'. Jake's loud groan confirmed her suspicions, it felt good for him. That was good, it boosted her arousal knowing that he was in so much pleasure, regaurdless of what she was feeling. She very slightly moved her hips against him, a soft noise slipping from her lips that could easily be read as pleasurable although it was more so in discomfort. He kept his hips moving, feeling her slight movements and he didn't mind that she wasn't moving a lot because he understood it was a bit uncomfortable.

She was going to have to toughen up and get through this better than what she was doing now because she felt terrible, she had wanted their first time to be better than this. He couldn't stop though, he had to keep going and she just had to get used to his huge cock. She just hoped that he didn't mind. Jake felt slightly guilty for being in such pleasure when Addison wasn't in just as much. He wanted her to be writhing in pleasure but it seemed that wouldn't be happening tonight which did suck but at least they would get their eventually, once he had been inside of her a few times and her walls adjusted an were able to stretch around his thickness. He made sure to move slowly but he had to move or else she would never adjust. He pressed his lips to hers, kissing her softly before deepening the kiss and pushing his tongue into her mouth. Addison sucked in a little breath, returning the kiss which was a good distraction technique. Her tongue moved against his, she knew that the more times they did this, the more and more she would adjust until she had absolutely no trouble in taking in his cock. Her hips moved just slightly against his, she didn't want to just lay there and make him do all of the work. He dropped a hand between their bodies and began to rub her clit. He wanted to help her and if she didn't orgasm during sex he would make sure she did afterwards. She gasped softly against his lips as his fingers made contact with her clit, but it wasn't a painful gasp this time, it was a pleasurable one. Clitoral stimulation was obviously a big get goer for her, without it she very rarely climaxed, they had a lot to learn about each others body though and Jake would learn that. Addison lifted her right leg, hooking it around his hip, allowing him deeper access, wanting him to get as much pleasure as possible.

Jake's lips merged with hers, kissing her passionately and hungrily as his tongue explored the inside of her mouth. One hand worked her clit, rubbing the nub in a circular motion and adding a bit of pressure every so often. He began to thrust a little harder, but not too much. She honestly felt so incredible he couldn't contain his pleasure as he moaned into her mouth. His free hand found her breast, cupping the perfect hand sized flesh in his hand and massaging it. When she lifted her leg, his cock slipped in further, deeper - his tip against her g-spot and he groaned loudly as he thrusted a bit faster. Addisonwas glad to hear him groaning in pleasure, knowing he was enjoying her body which was a huge relief for her, she had been a little worried. Her tongue moved against his, kissing him hungrily as his fingers rubbed against her clit perfectly and he cupped her small breast, massaging it. Her breasts didn't really respond to stimulation, sometimes it felt amazing, most of the time it wasn't something that aroused her though, but it was nice. His cock stroked deeper, hitting her g-spot and that felt good, a very soft moan slipping from her as he groaned loudly. She moved a hand between them, cupping his shaven balls, her slender fingertips massaging them lightly to add to his pleasure. She lived that he was shaven, she hadn't been expecting it, but she loved it.

Jake was finding out all the things she liked. He cottoned on quickly to the fact she loved her clit being played with. He didn't know her breasts didn't stimulate her as much but it didn't matter because her breasts did a lot for him. He flicked her nipple and kissed her harder, his cock delving so deeply into her tight hole and his tip pushing against her g-spot. The pleasure was intense for him and so he was beginning to thrust a little harder and faster too. The moment she made contact with his shaven balls had him groaning. He loved his balls being played with and most woman just ignored them but Addison, she was onto it and it was incredible. He pulled his lips from hers and moaned into the room. "Addison." He groaned, his thick and hard cock so jammed within her walls and it was amazing. It had been a long time since he had been with someone so tight like Addison was. Jake's thick cock really stretched her, she thought that Mark Sloan was huge, he had nothing on Jake. She continued to massage his balls, figuring out quickly that he definitely really liked when she did that and she really wanted to please him and bring him to his climax. She groaned softly as his thrusts got harder and faster, he was obviously in a lot of pleasure which was great, but it was uncomfortable for her, she was fine with it though, she wanted him to cum, she wanted him to be pleased and to reach his release. It wasn't everyday you came across a pussy as tight as Addison's so she would let him enjoy it. Plus, his moans and groans were a huge turn on.

Jake was definitely getting close, his impending release was on his way. He figured Addison would tell him if he was hurting her, he knew it was uncomfortable, kind of like her first time all over again he assumed. He had never really thought of his cock being big, he knew it was a bit thicker than others but no other woman he'd been with had really been like this - clearly Addison hadn't slept with a lot of men with large cocks even though she had slept with a few different men. It was fair enough to say that Addison had slept with a lot of men in her lifetime, but they had all been around average or below, none like Jake's thickness. "Addison." He groaned her name, his cock slipping in and out of her tightness and his balls beginning to tighten in her grasp as he rubbed her clit harder and faster. He was so close, he wanted to orgasm with her but he didn't think that was going to happen this time. He kept moving though, his moans growing in volume and he knew she would figure out he was about to cum. It was easy to tell that with his increased moans that he was very close, she could feel his balls tightening with in her hand and she moaned softly. "Mm, baby, cum for me." She whispered softly against his lips as her massaging of his balls increased and she tilted her hips up a little, she wasn't even close to climaxing but she was glad that he was.

With his balls tightening within her fingers, he groaned out loudly as his cum began to travel down his shaft and soon he exploded inside of her, coming out in thick spurts. Addison felt his large cum load spurting into her and she tightened her pussy walls around him, kind of simulating an orgasm. "Mmm." She continued to massage his tightening balls until he had finished filling her with his cum before she released his balls and smoothed her hands over his chest with a soft moan. He had quite a bit of a cum load being emptied into her and he was in pure pleasure as he kept rubbing her clit and his other hand gripped her thigh tightly, as he slowed his thrusts. She loved that he had a big cum load too, she couldn't really think about anything that she didn't like about him, he seemed so perfect. She just wished that she could have done more, but she'd have to wait a few more times before she was adjusted probably.

Jake groaned out, having emptied himself inside her tight hole and his cock now slowly becoming flaccid again. He slowly pulled his cock out of her pussy, his cum dripping a little from her and he rolled off her as he caught his breath and closed his eyes. "Wow." He mumbled. No doubt Addison would probably be a bit sore tomorrow, but right now he was reeling from the pleasure. "You're amazing. You're so amazing." He whispered leaning over to kiss her softly. "I'm sorry you didn't orgasm. But I promise you will soon." He winked. There was no way he would leave her without an orgasm because she would definitely cum. Addison could feel his cum dripping from her tight hole, coating her folds, trickling down between her ass cheeks, she was definitely very full of his cum. "Mm that's quite the cum load you got there." She smirked, her hand smoothing over his side lightly. She had been so worried that he would find sex with her terrible, but he was clearly pleased which was a great thing. "It's okay, I'm sorry I didn't cum with you baby, maybe next time?" She closed her legs, knowing she was definitely going to be sore in the morning, but grateful that he was concerned about her pleasure as well. It might be a while though until they were able to cum together, but she didn't mind, as long as he reached his climax. "Mm." She kissed him softly, brushing her lips against his lightly.

"For a moment with all the mishaps I didn't think we'd even make it to have sex." He admitted with a laugh, his cheeks red from both embarrassment and the heat of his body. Honestly, he hadn't thought his size would be a problem but clearly it was and would take some time.

She laughed softly, there did seem to be a lot in their way tonight. "Well, we made it to the sex after all, I'm sorry I'm so tight baby." He shook his head. "Don't be it's amazing to me I'm just sorry I'm so thick. I hope I didn't hurt you" He whispered.

Addison pecked his lips, giving him time to come down from the orgasm. "Mm I love that you came so much." Her fingers dipped between her folds and easily gathered a lot of his thick creamy cum on her fingers and she brought it to her lips, sucking them clean. She could taste a lot of the lube, having been very lubed up, but she also got the taste of his cum, moaning softly. She wasn't like most other women who were squimish over cum and blowjobs - she loved it. Jake watched Addison, his eyes widened a little as her fingers gathered his cum and she licked it off. "you're the sexiest woman...ever" He decided. There was no one like her she was amazing. "Your moan is so sexy. Like when you eat ice cream." He smirked playfully. "and, you're so tight and sexy of course I would cum a lot." He winked of course saying the amount he had cum was because of how much she turned him on, but he always just had a massive cum load. He rubbed her side lightly and kissed her softly, closing his eyes as he just gathered himself from the intense orgasm.

"I love your cum." She whispered softly with a mischevious smile, licking her lips. She didn't know what he had eaten but his cum was actually quite sweet, of coarse it was still salty, but instead of being bitter, it had a deliciously sweet taste to it. "Mm, well now I want to taste your cum." Jake whispered in return, his hand cupping her cum filled pussy, causing her back to arch and for her to moan out softly, his thumb finding her clit, flicking against the sensitive nub. Addison bit down on her bottom lip. "Two fingers, baby." She didn't want too much filling her, she didn't want to be too sore tomorrow, she would be sore enough as it was after taking his monsterous cock.

"I'll be gentle gorgeous" He whispered as he moved down between her legs, spreading them and getting a good look at her amazing pussy. He licked his lips as he got down and used his tongue to run between her creamy folds. He wanted to get her wet again to wash away some of his cum and replace it with her own juices though he didn't care if he tasted his own. Lowering his head he attached his lips to her clit and sucked softly, her back arching slightly and her legs spreading for him. He slowly pushed two fingers into her, it was easy because she was wet, there was still lube reminants and his cum was making her folds slippery.

Addison tucked a hand underneath her own head comfortably as she watched him working her pussy, his mouth and tongue doing wonders on her clit, his fingers starting to thrust in and out of her tight, slick pussy. His fingers simply thrusted softly and slowly for a while whilst he gently sucked on her clit, but then he upped the tempo, his fingers moving quicker, his tongue swirling around her clit as she started to pant softly in pleasure. She wouldn't take long to get to an orgasm at all. His teeth lightly locked around the sensitive nub and he sucked a little more firmly, flickering his tongue against his whilst he curled his fingers to reach her g-spot, easily reaching and stimulating it very skillfully.

It was Jakes job to know a woman's vagina. And he definitely knew it. He kept his two fingers curved a little as his lips worked her clit keeping her stimulated constantly as he sucked and thrusted all at once. Addison's hips twitched a little more, more moans slipping from her lips as he pleasured her. "Harder." She mumbled softly as she watched him working her pussy, with just his fingers inside of her, she could handle a lot more roughness and she definitely wanted it harder and faster which would make her squirm and writh with pleasure. There were a lot of perks in having a boyfriend who had medically examined your vagina because Jake really knew her vagina which would make for great sex.

Jake mumbled against her clit, hearing her request he began to go harder and faster with his fingers and his sucking. He moved his lips down, sucking on her folds now as his other hand found her clit and began to rub at it roughly. "Mmm" He moaned against her before pulling his fingers out and replacing them with his tongue. He pushed his tongue in deep, getting a good taste of her and licking around her walls before thrusting the muscle in and out. Addison moaned loudly, her hips writhing in pleasure as he started to rub against her clit with his fingers, his tongue in her folds and entrance. "Mmm oh." She moaned as her hand rubbed over her stomach and down to his head, her fingers tangling in his hair. "That's so good." She praised. Jake smiled against her pussy, kissing her entrance and thrusting his tongue while she moaned and writhed in pleasure. It was so hot hearing her moan and he quickly picked up the pressure on her clit, rubbing harder with his thumb in a clockwise direction while his tongue did the rest of the work.

Addison arched her back, her features contorted in pleasure as she closed her eyes, moaning and concentrating on the pleasure, her pussy throbbing. "Mmmmmm." She squirmed beneath him, curling her toes as she got pushed closer and closer to the edge. Jake moaned as he soon hooked his arms around her thigh and pulled her in close, with her back arched like that he was able to push his tongue in completely, flicking against her walls. He soon moved his mouth up again, sucking her pussy and up to her clit. He could tell she was close and he was so excited for her to cum that his cock was beginning twitch again. Addison's breathing got heavier, her moans repetitive as his mouth sucked on her pussy, it felt amazing, it had been a while since she had gotten oral sex like this, he was amazing. Her walls tightened, squeezing and pulsating, as her orgasm hit, her hips rising and jerking off of the bed as she released a series of long moans. Her orgasm was intense, her mouth hanging open with moans as her walls contracted and pushed her cum and juices, mixed with his, out of her pussy, pooling within her folds as she squirmed and moaned, her skin flushing a deep pink colour.

"Mmm." She moaned and opened her eyes again to watch him lapping at her pussy and she licked her lips, her hips and muscles relaxing again as she slowly came down from the orgasm and she pushed his hand away from her extremely sensitive clit - he really wouldn't be able to touch it for a while as she got very sensitive after an orgasm. "Mm god your so amazing." She relaxed her legs against the bed as she smiled down at him dreamily, running her fingers through his hair. "That was wonderful." She praised her boyfriend, earning a grin from him.

Jake slowly sat himself up, licking around his lips as they were glossed with her juices and he moved back up to her side. He knew not to touch her clit now, she was bound to be sensitive and it would probably earn him a kick in the head and he didn't feel like that. He smiled at her, pulling her into his arms and kissed her temple. "You're more amazing." He whispered.

Addison was quite limp after her orgasm, easily pulled into his arms, her head resting on his chest, her red hair sprawled out messily as she came down from her orgasm. She just rested against him, her eyes closing lazily, content with her orgasm. "God that was great." She smiled dreamily. "It was really something." He whispered, kissing the top of her head. Jake couldn't believe they had made it here and yes there had been many bumps in the road of course just getting to the bedroom had proved a difficult task. "Mm, Sam is going to wonder why you're walking so funny tomorrow." He smirked. He actually felt good about it because Sam was a bit of a jerk and he was a complete idiot for letting somebody like Addison go and for treating her like crap when they were together. Jake would cherish every moment he had with the beautiful red head, he would cherish the ground she walked on. He had that overwhelming feeling to give her everything she had ever wanted, to love her unconditionally, to give her a baby, to marry her, settle down with her, have grandbabies with her. But most of all, he wanted to give her the happily ever after she had always sought for and deserved.


End file.
